Water → 7-chloro-3-(2-methylsulfonylaminobenzenesulfonyl)-2,4(1H,3H)-quinazolinedione

HRID 2301293Notes

Reaction equation

HRID 2301293 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:23])(=[O:10])=[O:9].[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>N1C=CC=CC=1>[Cl:22][C:16]1[CH:15]=[C:14]2[C:19]([C:20](=[O:21])[N:11]([S:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][S:25]([CH3:24])(=[O:27])=[O:26])(=[O:10])=[O:9])[C:12](=[O:23])[NH:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 98413923-(2-Aminobenzenesulfonyl)-7-Chloro-2,4(1H,3H)-Quinazolinedione

Product 1

HCID 98673267-chloro-3-(2-methylsulfonylaminobenzenesulfonyl)-2,4(1H,3H)-quinazolinedioneYield 66.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

22 mg (0.06 mmol) of Compound 2 was dissolved in 200 μl of pyridine, 11.6 μl (0.15 mmol) of methanesulfonyl chloride was added dropwise, then the resultant mixture was stirred at room temperature overnight. An excess amount of water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N aqueous hydrochloric acid solution and saturated saline, then dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. The crude product was crystallized from diethyl ether to obtain 16 mg (0.04 mmol) of the above-identified compound. Properties: colorless crystal, Melting point: >200° C. (decomposition), PMR (δ ppm, DMSO-d6): 3.61 (3H, s), 7.10 (1H, d), 7.20 (1H, d), 7.74 (1H, d), 7.82-7.90 (4H, m), 8.34 (1H, d), 11.70 (1H, s).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N aqueous hydrochloric acid solution and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain a crude product
  6. customThe crude product was crystallized from diethyl ether

Sources & evidence

ORD record
ord-45b8741254a24b13bb639c878acb4d03
Source dataset
uspto-grants-2002_12
Patent number
US06500835B2

Reaction notes

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